Institut Galien Paris-Sud, CNRS UMR 8612, Université Paris-Saclay, Faculté de Pharmacie, 5 rue JB Clément, 92296 Châtenay-Malabry, France.
Institut de Chimie Moléculaire et des Matériaux d'Orsay, CNRS UMR 8182, Université Paris Saclay, Bâtiment 420, 91405 Orsay, France.
Molecules. 2020 Mar 24;25(6):1459. doi: 10.3390/molecules25061459.
Nanoformulated calix[8]arenes functionalized with -heterocyclic carbene (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4'-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance.
功能化的杯[8]芳烃纳米反应器,其表面负载了 -杂环卡宾(NHC)-钯配合物,可在水中高效催化水溶性碘代和溴代芳基化合物与环状三醇芳基硼酸酯的 Suzuki-Miyaura 交叉偶联反应,在低温下无需添加任何有机溶剂。结合三醇芳基硼酸酯的一步法合成,这一高效的新工具在低催化剂负载量下,以良好的收率实现了多种 4'-芳基化苯丙氨酸和酪氨酸的合成,具有广泛的官能团容忍度。